Azo dye and process of making same.



To 0123 whom Be it know itnine and or methyl grmip, in

5 (thus, for

obined W4 5. to coloring matters whic es pi her, to 0 lo es possgei ist the action of oiuhle in. oil. The

d hose with heteout in the .4 of acetate and, it desciii, or soap, may i w sect-ion may he made to a gz-resence er s substratum.

l-2-nitrsnilin used in no, is obtainable nitoioid. en l ssponiiying I i yt-chior 5-methy -6-nitw the some time can be on i separated, it much more easily sol] in alcohol the 4-chlo1z-5-meth i iitrnnilin. This 4iehlor 5-xnethyl-2-nitmr 11 consists of yeliowish brown prisms which melt about 159 C.

The derivatives of ortho-ni renilin which we use according to our invention can he represented by the fornniie where and Y me.y each represent either ehlon'n or methyl.

scifieetion 0:? Letters Eeten many, have in in A150 @Fhiilit NET FUSSENEGGER, OF LUDWIGSHAFEN-ON-THE-RHINE, AND LOUIS QFLIIEZM, GERMANY, ASSEGNORS TO BADISOHE ANILIN & SODA FA BRIK, II-Gl Z-QHEJtHINE, GERMANY, A CORPORATION.

Patented Hey 11, Eerie? 1 -570. ifi-250.

The coloring-matters produced according to our invention possess oran e-red shades, ere insoluble in Water and in diets acids and nllialies, and upon reduction with tin and hydrocl'iloric acid yield Leminc-Q-nephthol and a i.2-diemino-benzol derivative possessing a constitution represented by the general formmo- Where X and Y may each represent either chlorin or methyl.

The followingexamples will serve to illustrete further the nature of our invention, which, however, is not confined to these exam les. The arts are by Weight.

'Xnmple 1: ntroduce twenty and seventenths parts of 4.5-dichlon2-nitrsnilin into ,asolution of seven parts of sodium nitrite in one hundredparts of concentrated sulfuric acid, and, when diazotization is complete, pour the mixture on two hundred parts of ice, filter the solution, if necessary, and-allow it to run, While Well stirring, into a freshly prepared suspension of fifteen parts of betsnaphthol. When the combination is complete, .filter ofi the vcoloring matter, and Weshit.

Example 2 Diezotize thirty-seven and one-hnifpsrts of e-methyl-fii-chlor-2-nitrenilin in the usual Way, filter the disco solution, if necessary, and allow it to run, While stirring well and at :1 temperature of zero centig'rede, into an aqueous suspension of twentynine parts of hete-nephthol to which anexcess of sodium acetate has been added. The suspension is preferably prepared by dissolving the beta-nephthol in caustic soda solution and precipitating it by means of acetic acid. 9 When the, comhinstion is completmfilter off the coloring matter and wash it. In 2:, simii lsr manner -chlor-fi-methyl-Z-nitrsnilin can be made to yield the corresponding coloring wetter,

E on? what we claimisz- 1. The process of making ezo coloring terby combining with betamaphthol a (liazetized ortho-nitrenilin derivative possess ing a constitution represented hy the hereinhefore defined formula v tho-nitrenilin'(lerivutive possessing a constitution represented by the hereinbeiore defined formula NHL. (\INO: x

which coloring matters possess orange-red shades, are insoluble n water and in dilute acids and alkelies, and upon reduction with,

tin and hydrochloric acid yield Lamina-2- nephthol and a. 1.2-die1nin0-ben2ol derive-- tlve possesslng & constitution.represented by the herelnbefore defined formula,

4; As a new article of manufacture the colering; matter which can be obtained by eon:- bini'ng cliazotized 4 5-diehlor-2-nitra-nilin with beta-naphthol, which coloring matter possesses an orange-red shade, is insoluble in water and in dilute acids and alkalies, and upon reduction with tin and hydrochloric avid yields l-emino-Z-naphthol and 4.5- dichlor-Z-nitrenilin.

In testimony whereof we have hereunto set our hands in the presence of two subscribing witnesses.

PAUL JULIUS. ERNST FUSSENEGGER.

LOUIS BLANGEY. Witnesses: v

J. ALEO. LLOYD,

TERESA CATTARAM. 

